Philip Seymour Hoffman is the only actor I can think of that can be described as “creepy” or “a pervert,” and it’s meant as a compliment. He’s a dependably fantastic actor who can play the lead (Capote), the bully who hates yahoo touchers, (My Boyfriend’s Back), the drugged-out journalist (Almost Famous), the assistant (The Big Lebowski), the guy who gets set on fire while in a wheelchair (Red Dragon), the villain (Mission: Impossible III), and the guy who has sex with Marisa Tomei in the first scene of a movie (Before the Devil Knows You’re Dead), all with equal aplomb. But mostly, he’s the creepy dude.
In honor of The Master, which teams PSH with director Paul Thomas Anderson for the fifth time, here are the eight creepiest roles in Philip Seymour Hoffman’s creepy career.
Some might argue that Truman Capote was more quirky, possibly eccentric, than creepy, but I disagree. It’s not just the giggly, effeminate lisp, either — it’s the way he never felt like an actual person, like he was a character out of one of his stories. PSH captured that remarkably in Capote. He was a walking tragedy, someone who was so torn up and self-loathing inside that late in life, he got a facelift. Capote isn’t a great movie, but PSH’s performance is haunting. Also, the lisp.

If anyone’s ever been meant to play a phone sex-line supervisor, it’s PSH. He doesn’t have much of a part in Punch-Drunk Love, a film people don’t give nearly enough credit to, but he DOES get to yell “shut the f*ck up” to Adam Sandler, something we’ve all wished for at one point in our lives.

Sandy Lyle, not to be confused with the Scottish golfer of the same name, is a former-child actor who looks and acts the way all former-child stars do (and should): like the world owes him something, despite his unkempt, piggish appearance and crude personality. FUN FACT: Along Came Polly is one of only two movies to feature a ferret and the word “sharted.”
The other, of course, being Fellini’s 8 1/2.

Wearing stiff khakis and a New York Yankees cap, the look of any professional introvert, high school teacher Jacob Elinsky meets his friend Monty Brogan (Edward Norton), who’s about to serve a seven-year prison sentence, at a hip city club. Who else is at the club? His gap-toothed crush, Mary D’Annunzio (Anna Paquin), who’s also his student and in 11th grade. Things get weird(er) when he follows her upstairs.

Flawless really should have been the perfect movie (without flaws, if you will). It certainly had the right ingredients: Robert De Niro as a cop named Walter Koontz…living in a building with drag queens…including PSH’s Rusty, who wants to become a transvestite…and helps Koontz after he’s shot and becomes paralyzed…something something in French Bob Dole…with a song from Cher…as directed and written by Batman & Robin‘s Joel Schumacher. But the finished product was a total mess, which is a shame — it’d be great if De Niro became a drag queen idol. He could go by Jake That’sLaMottaMan.

In the Oscar-nominated Doubt, Hoffman plays a Catholic priest, Father Brendan Flynn, who’s been accused of touching little boys in their pope-pope zone. The fact that a pedophiliac priest isn’t ranked as the creepiest role of Hoffman’s career either says a lot about me or a lot about Hoffman, though the fact that I laughed at this clip ending with “Maybe take the boys on a camping trip” probably means me.

Boogie Nights is a perfect movie, and PSH’s Scotty J. is a big reason why. He’s a gay boom operator who steals an awkward, long-desired-for smooch from Dirk Diggler (Mark Wahlberg), and after his advances halted, goes into his car and calls himself a “f*cking idiot” over and over again. He’s a disaster of a human being, though one with a killer fashion sense.

Allen, who really posses the ol’ Wiggum charm, is in love with his next door neighbor, Helen (Lara Flynn Boyle). He’s also a prodigious maker of anonymous phone calls that end with grunts and moans. He accidentally calls Helen one day, but she likes the idea of a random guy jerking off to her over the phone. She eventually (and dispassionately) finds out that the man who’s been calling her is Allen, though, and he sinks into depression. So he calls someone else, Helen’s sister Joy (Jane Adams), and pretends to be “Damien.”
It’s the role he was born to play.

And I can’t be the only one who does “drunk Scotty” now and then to make people laugh (whether I’m drunk or not)….sometimes I’ll just look at my wife and say “I wanted to make sure you thought it was cool or Iwasgonnatakeitback”

First film I think I ever saw him in was The Talented Mister Ripley and although that is an absolutely brilliant film it has ruined him for me forever as he is just SO creepy in it because of that little laugh he does and the way he seems to overly consider everything he says. Gives me the heebies.